Chicago to San Juan flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$203 is $125 (38%) below the usual $328 for Chicago → San Juan.
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when Chicago → San Juan drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $203 (cheapest month) |
| November 2026 | $226 |
| December 2026 | No fares found yet |
| January 2027 | $386 |
| February 2027 | No fares found yet |
| March 2027 | $428 |
| April 2027 | $329 |
| May 2027 | No fares found yet |
| June 2027 | $328 |
| July 2027 | $236 |
Cheapest dates in the next 4 months
Round trip, per person-
Oct 23 – 26 3 nights · leave Fri$203 −38% vs usual$203 −38% vs usual Book
Frontier Airlines 1 stop · 6h 18m -
Nov 2 – 10 8 nights · leave Mon$226 −31% vs usual$226 −31% vs usual Book
Frontier Airlines 1 stop · 6h 11m
-
Oct 16 – 19 3 nights · leave Fri$228 −30% vs usual$228 −30% vs usual Book
Frontier Airlines 1 stop · 5h 55m
-
Oct 13 – 22 9 nights · leave Tue$236 −28% vs usual$236 −28% vs usual Book
Frontier Airlines 1 stop · 5h 59m
-
Oct 15 – 19 4 nights · leave Thu$236 −28% vs usual$236 −28% vs usual Book
Frontier Airlines 1 stop · 5h 57m
-
Oct 12 – 22 10 nights · leave Mon$279 −15% vs usual$279 −15% vs usual Book
American Airlines 1 stop · 5h 51m -
Nov 13 – 16 3 nights · leave Fri$310 −5% vs usual$310 −5% vs usual Book
Frontier Airlines 1 stop · 6h 06m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Plan the rest of your trip
San Juan · Oct 23 – 26Travel insurance · EKTA Airport transfer · Kiwitaxi
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Good to know
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Chicago to San Juan: questions
How much is a flight from Chicago to San Juan?
The cheapest round trip we have found right now is $203, leaving October 23 and returning October 26. The usual price on this route is about $328, so this fare is 38% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Chicago to San Juan?
October 2026, with round trips from $203. The most expensive month in our data is March (from $428). Based on the 7 months ahead we have prices for.
About this route
We track round-trip economy fares from Chicago (United States) to San Juan (Puerto Rico) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $203, departing October 23 and returning October 26, about 38% below the usual $328. Right now we're following 7 upcoming date combinations on this route. The cheapest month to fly in our data is October, from $203. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.